4 Beds, 2 Baths, 2,148 sq ft
1860 Vía Contessa
Winter Park, FL 32789
-
Bedrooms
8
-
Bathrooms
6
-
Square Feet
7,000 sq ft
-
Available
Available Now
About This Home
Step into your dream home in Winter Park! This stunning 7,000 SF residence, nestled on a peaceful street in the coveted Vias neighborhood, offers ample space across three levels, making it an ideal choice for those who crave both room to spread out and a welcoming atmosphere. Gorgeous hardwood floors flow throughout the main living areas, enhancing the home's inviting, warm ambiance. The open-concept design seamlessly blends living spaces, perfect for both intimate family moments and large gatherings. The chef-inspired kitchen is the heart of the home, featuring 42-inch cabinets, gleaming quartz countertops, a gas range, and double ovens. The oversized eat-in bar and cozy dining area flow into the spacious family room, keeping the chef engaged with guests at all times. This home offers two expansive primary suites, each providing a peaceful, private retreat. The first and second floors, covering 4,500 SF, include five bedrooms and four baths, while the lower level adds a 2,500 SF in-law suite, complete with a spacious primary bedroom, ensuite bath, two secondary bedrooms, a full hallway bath, kitchenette/bar, gym, large living room, and more. Whether you need a quiet hideaway, home office, entertainment space, or hobby room, thishome offers endless possibilities. The main floor showcases a thoughtfully designed layout with a private main suite, elegant living and dining areas, and a cozy family room with a gas fireplace. French doors lead to the covered rear patio and pool deck, blending indoor and outdoor living. The well-appointed main suite boasts a luxurious bath and custom walk-in closet. Upstairs, you’ll find four bedrooms, two Jack-and-Jill baths with double sinks, a large laundry room, and a versatile studio/playroom. Custom loft stairs lead to a third-floor bonus space, perfect for kids’ playtim eor creative pursuits. The lower level is a true standout, offering 2,500 SF of flexible space. It includes a private living area, kitchenette, breakfast bar, a generously sized primary bedroom with ensuite, two additional bedrooms, a gym, a workshop area, and a game room complete with a pool table. Large window wells bring in natural light, and the space has direct access to the back patio and pool deck. Located in a quiet cul-de-sac, just minutes from Park Avenue and a short walk to the Winter Park Racquet Club, this exceptional home is in the highly sought-after Dommerich/Maitland/Winter Park High School district. Don’t miss the opportunity to make this residence your own and fulfill your vision of the perfect Winter Park lifestyle! All measurements and dimensions should be verified
1860 Vía Contessa is a house located in Orange County and the 32789 ZIP Code. This area is served by the Orange County Public Schools attendance zone.
Fees and Policies
The fees listed below are community-provided and may exclude utilities or add-ons. All payments are made directly to the property and are non-refundable unless otherwise specified. Use the Cost Calculator to determine costs based on your needs.
-
One-Time Basics
-
Due at Move-In
-
Security Deposit - RefundableCharged per unit.$10,000
-
-
Due at Move-In
Property Fee Disclaimer: Based on community-supplied data and independent market research. Subject to change without notice. May exclude fees for mandatory or optional services and usage-based utilities.
House Features
- Washer/Dryer
- Washer/Dryer Hookup
- Dishwasher
- Balcony
Contact
- Listed by Sierra Realty Group, LLC
- Phone Number
- Contact
Nestled in Central Florida, Winter Park combines historic charm with cultural amenities. Tree-lined brick streets wind through the city, where live oaks draped with Spanish moss create a natural canopy over the downtown area. Park Avenue serves as the city center, offering boutiques, cafes, and art galleries, while Rollins College enhances the community's educational landscape. The city's chain of lakes, connected by scenic canals, provides opportunities for water activities, and Mead Botanical Garden spans 47.6 acres of natural beauty. Current rental trends show moderate stability, with one-bedroom apartments averaging $1,482 per month and two-bedroom units at $1,766, reflecting slight increases of 0.7% and 0.6% respectively over the past year.
The rental market in Winter Park features properties ranging from lakefront apartments to garden-style communities near Park Avenue.
Learn more about living in Winter Park- Washer/Dryer
- Washer/Dryer Hookup
- Dishwasher
- Balcony
| Colleges & Universities | Distance | ||
|---|---|---|---|
| Colleges & Universities | Distance | ||
| Drive: | 7 min | 2.8 mi | |
| Drive: | 8 min | 3.0 mi | |
| Drive: | 11 min | 4.3 mi | |
| Drive: | 13 min | 4.8 mi |
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
View GreatSchools Rating Methodology
Data provided by GreatSchools.org © 2026. All rights reserved.
You May Also Like
Similar Rentals Nearby
-
$2,500Total Monthly PriceTotal Monthly Price NewPrices include all required monthly fees.12 Month LeaseHouse for Rent
-
$3,250Total Monthly PriceTotal Monthly Price NewPrices include all required monthly fees.12 Month LeaseHouse for Rent
4 Beds, 2 Baths, 1,700 sq ft
-
-
-
-
Total Monthly Price New4 Beds$2,537+5 Beds$4,635+Total Monthly PricePrices include base rent and required monthly fees of $130. Variable costs based on usage may apply.Base Rent:4 Beds$2,407+5 Beds$4,505+
-
-
-
4 Beds$2,550Total Monthly PriceTotal Monthly Price NewPrices include all required monthly fees.House for Rent
-
What Are Walk Score®, Transit Score®, and Bike Score® Ratings?
Walk Score® measures the walkability of any address. Transit Score® measures access to public transit. Bike Score® measures the bikeability of any address.
What is a Sound Score Rating?
A Sound Score Rating aggregates noise caused by vehicle traffic, airplane traffic and local sources